10. Dean Malenko
Of the four Radicalz who jumped from WCW to WWE in 2000, Dean Malenko was always the least likely to succeed long-term. A flawless in-ring technician, he was undersized, lacked the charisma and microphone skills required to excel in sports entertainment’s upper echelons, and struggled to establish a lasting connection with the WWE faithful.
His failure wasn’t entirely his own fault, however. Malenko was set to wrestle The Godfather shortly after the Radicalz’ reformation later in 2000, but was offered one of Godfather’s escorts instead of wrestling him. Dean accepted, and the ridiculous “Double Ho Seven” gimmick was born, transforming the ice cold grappler into a clumsy James Bond parody act.
The following weeks saw Malenko compete for Lita’s affections, even going so far as offering her a match for his Light Heavyweight Championship. Lita lost, forcing her to go on a date with Malenko, who drifted into a brief feud with Jacqueline and Ivory afterwards. Grossly ill-suited to playing a lecherous womaniser, Malenko’s career was systematically destroyed by the intergender storylines, and he quietly retired in 2001.